#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:07:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179614 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/78/4507898.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4507898
loop_
_publ_author_name
'Gilli, Gastone'
'Bertolasi, Valerio'
'Gilli, Paola'
_publ_section_title
;
 Solid-State N--H···O/O--H···N
 Tautomerism in Resonance-Assisted 1-(Arylazo)-2-Naphthols and Its
 Through-Spaceπ* ← \pPerturbation in TCNQ Cocrystals. A
 Variable-Temperature X-ray Crystal Study
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3308
_journal_paper_doi               10.1021/cg301546v
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C17 H14 N2 O, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C23 H16 N4 O'
_chemical_formula_weight         364.40
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.2758(12)
_cell_angle_beta                 97.5236(11)
_cell_angle_gamma                103.5853(12)
_cell_formula_units_Z            2
_cell_length_a                   7.6863(2)
_cell_length_b                   9.9399(3)
_cell_length_c                   12.7007(4)
_cell_measurement_reflns_used    9616
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.33
_cell_volume                     908.93(5)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9616
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0752P)²+0.1528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                4025
_reflns_number_total             5238
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301546v_si_002.cif
_cod_data_source_block           2-T150
_cod_database_code               4507898
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.42973(12) 0.76539(10) 0.06132(7) 0.0350(2) Uani 1 1 d
N1 N 0.06886(13) 0.69664(9) 0.10728(8) 0.0246(2) Uani 1 1 d
N2 N 0.08524(13) 0.68561(10) 0.00472(8) 0.0253(2) Uani 1 1 d
C1 C 0.22043(15) 0.73850(11) 0.18358(9) 0.0238(2) Uani 1 1 d
C2 C 0.40388(16) 0.77284(12) 0.15850(10) 0.0274(2) Uani 1 1 d
C3 C 0.55607(16) 0.81813(13) 0.24913(11) 0.0318(3) Uani 1 1 d
C4 C 0.53039(16) 0.83028(13) 0.35333(11) 0.0304(3) Uani 1 1 d
C5 C 0.35119(16) 0.79612(12) 0.38084(10) 0.0271(2) Uani 1 1 d
C6 C 0.19615(15) 0.74968(11) 0.29646(9) 0.0245(2) Uani 1 1 d
C7 C 0.32971(18) 0.80899(14) 0.49033(10) 0.0344(3) Uani 1 1 d
C8 C 0.1588(2) 0.77688(17) 0.51669(11) 0.0413(3) Uani 1 1 d
C9 C 0.00469(19) 0.73073(16) 0.43286(11) 0.0390(3) Uani 1 1 d
C10 C 0.02290(16) 0.71685(13) 0.32506(10) 0.0312(3) Uani 1 1 d
C11 C -0.07061(15) 0.64367(11) -0.07775(9) 0.0231(2) Uani 1 1 d
C12 C -0.24677(16) 0.61747(12) -0.05492(10) 0.0262(2) Uani 1 1 d
C13 C -0.39394(16) 0.57911(12) -0.14106(10) 0.0274(2) Uani 1 1 d
C14 C -0.36959(16) 0.56722(11) -0.24940(10) 0.0276(2) Uani 1 1 d
C15 C -0.19255(17) 0.59240(12) -0.26997(9) 0.0278(2) Uani 1 1 d
C16 C -0.04309(16) 0.63097(12) -0.18541(10) 0.0267(2) Uani 1 1 d
C17 C -0.5303(2) 0.52933(15) -0.34160(11) 0.0366(3) Uani 1 1 d
H1 H 0.208(3) 0.707(2) -0.0124(16) 0.059(5) Uiso 1 1 d
H3 H 0.681(2) 0.8381(16) 0.2284(13) 0.038(4) Uiso 1 1 d
H4 H 0.637(2) 0.8643(17) 0.4153(14) 0.043(4) Uiso 1 1 d
H7 H 0.443(2) 0.8403(17) 0.5480(14) 0.043(4) Uiso 1 1 d
H8 H 0.145(3) 0.789(2) 0.5931(17) 0.061(5) Uiso 1 1 d
H9 H -0.119(3) 0.7109(19) 0.4542(15) 0.054(5) Uiso 1 1 d
H12 H -0.264(2) 0.6270(15) 0.0237(12) 0.032(4) Uiso 1 1 d
H15 H -0.172(2) 0.5832(16) -0.3443(13) 0.035(4) Uiso 1 1 d
H13 H -0.517(2) 0.5650(16) -0.1241(13) 0.039(4) Uiso 1 1 d
H16 H 0.084(2) 0.6513(16) -0.2009(13) 0.035(4) Uiso 1 1 d
H171 H -0.536(3) 0.438(2) -0.3917(17) 0.067(6) Uiso 1 1 d
H172 H -0.523(3) 0.602(3) -0.383(2) 0.084(7) Uiso 1 1 d
H173 H -0.646(3) 0.528(2) -0.3143(19) 0.081(7) Uiso 1 1 d
H20 H -0.090(2) 0.6827(17) 0.2674(14) 0.044(4) Uiso 1 1 d
N1A N 0.61594(14) 1.14933(12) 0.18591(9) 0.0351(3) Uani 1 1 d
N2A N 0.19499(15) 1.10479(12) 0.38106(9) 0.0359(3) Uani 1 1 d
C1A C 0.13787(14) 1.04331(10) 0.09494(8) 0.0201(2) Uani 1 1 d
C2A C 0.18417(14) 1.03383(11) -0.01253(9) 0.0228(2) Uani 1 1 d
C3A C -0.05274(14) 1.00816(11) 0.10278(9) 0.0225(2) Uani 1 1 d
C4A C 0.27112(14) 1.08307(11) 0.18766(9) 0.0223(2) Uani 1 1 d
C5A C 0.46240(15) 1.11955(11) 0.18455(9) 0.0249(2) Uani 1 1 d
C6A C 0.22697(15) 1.09427(12) 0.29457(9) 0.0251(2) Uani 1 1 d
H2A H 0.313(2) 1.0570(16) -0.0179(12) 0.033(4) Uiso 1 1 d
H3A H -0.088(2) 1.0165(15) 0.1758(12) 0.031(4) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 N1 C1 118.41(10) . .
N1 N2 C11 120.17(9) . .
N1 N2 H1 118.4(12) . .
C11 N2 H1 121.4(12) . .
N1 C1 C6 116.65(10) . .
N1 C1 C2 123.36(10) . .
C6 C1 C2 119.99(9) . .
O1 C2 C3 120.78(11) . .
O1 C2 C1 121.59(10) . .
C3 C2 C1 117.62(10) . .
H3 C3 C4 123.3(9) . .
H3 C3 C2 115.3(9) . .
C4 C3 C2 121.41(11) . .
H4 C4 C3 120.6(9) . .
H4 C4 C5 117.1(9) . .
C3 C4 C5 122.36(11) . .
C7 C5 C6 119.84(11) . .
C7 C5 C4 120.78(10) . .
C6 C5 C4 119.37(11) . .
C10 C6 C5 118.44(11) . .
C10 C6 C1 122.33(10) . .
C5 C6 C1 119.23(10) . .
H7 C7 C8 121.4(10) . .
H7 C7 C5 117.7(10) . .
C8 C7 C5 120.83(11) . .
H8 C8 C7 120.3(12) . .
H8 C8 C9 120.3(12) . .
C7 C8 C9 119.33(12) . .
H9 C9 C10 121.4(11) . .
H9 C9 C8 117.9(11) . .
C10 C9 C8 120.71(12) . .
H20 C10 C9 118.5(10) . .
H20 C10 C6 120.7(10) . .
C9 C10 C6 120.84(11) . .
C16 C11 C12 120.49(10) . .
C16 C11 N2 117.11(10) . .
C12 C11 N2 122.39(10) . .
H12 C12 C13 121.6(8) . .
H12 C12 C11 119.5(8) . .
C13 C12 C11 118.89(11) . .
H13 C13 C12 118.4(9) . .
H13 C13 C14 120.0(9) . .
C12 C13 C14 121.61(11) . .
C15 C14 C13 118.31(10) . .
C15 C14 C17 120.70(11) . .
C13 C14 C17 120.98(11) . .
H15 C15 C16 118.6(9) . .
H15 C15 C14 120.2(9) . .
C16 C15 C14 121.23(11) . .
H16 C16 C15 120.6(9) . .
H16 C16 C11 119.9(9) . .
C15 C16 C11 119.45(11) . .
H172 C17 H171 108.4(18) . .
H172 C17 H173 102.2(19) . .
H171 C17 H173 112.4(18) . .
H172 C17 C14 111.8(14) . .
H171 C17 C14 110.0(12) . .
H173 C17 C14 111.8(14) . .
C4A C1A C3A 120.62(9) . .
C4A C1A C2A 121.25(9) . .
C3A C1A C2A 118.13(9) . .
H2A C2A C3A 121.1(9) . 2_575
H2A C2A C1A 118.2(9) . .
C3A C2A C1A 120.74(9) 2_575 .
H3A C3A C2A 119.2(9) . 2_575
H3A C3A C1A 119.6(9) . .
C2A C3A C1A 121.13(10) 2_575 .
C1A C4A C6A 121.75(9) . .
C1A C4A C5A 122.91(10) . .
C6A C4A C5A 115.32(9) . .
N1A C5A C4A 177.64(12) . .
N2A C6A C4A 178.68(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2665(15) .
N1 N2 1.3108(14) .
N1 C1 1.3373(14) .
N2 C11 1.4043(14) .
N2 H1 0.98(2) .
C1 C6 1.4560(16) .
C1 C2 1.4629(16) .
C2 C3 1.4468(16) .
C3 H3 1.012(16) .
C3 C4 1.3498(18) .
C4 H4 1.001(18) .
C4 C5 1.4448(17) .
C5 C7 1.4064(18) .
C5 C6 1.4125(15) .
C6 C10 1.4073(17) .
C7 H7 1.002(18) .
C7 C8 1.379(2) .
C8 H8 0.98(2) .
C8 C9 1.4037(19) .
C9 H9 1.005(19) .
C9 C10 1.3779(18) .
C10 H20 1.000(18) .
C11 C16 1.3967(16) .
C11 C12 1.3971(16) .
C12 H12 1.014(15) .
C12 C13 1.3900(16) .
C13 H13 0.981(16) .
C13 C14 1.3987(17) .
C14 C15 1.3933(17) .
C14 C17 1.5064(16) .
C15 H15 0.968(16) .
C15 C16 1.3889(16) .
C16 H16 1.004(16) .
C17 H172 0.97(3) .
C17 H171 0.99(2) .
C17 H173 1.00(2) .
N1A C5A 1.1442(15) .
N2A C6A 1.1471(15) .
C1A C4A 1.3798(14) .
C1A C3A 1.4456(14) .
C1A C2A 1.4461(14) .
C2A H2A 0.976(16) .
C2A C3A 1.3491(15) 2_575
C3A H3A 0.994(15) .
C3A C2A 1.3491(15) 2_575
C4A C6A 1.4321(15) .
C4A C5A 1.4370(15) .
